WO2009012201A3 - Procédé de préparation de sulfonamides de trifluoroalkyl-phényle et hétérocycliques - Google Patents

Procédé de préparation de sulfonamides de trifluoroalkyl-phényle et hétérocycliques Download PDF

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Publication number
WO2009012201A3
WO2009012201A3 PCT/US2008/069934 US2008069934W WO2009012201A3 WO 2009012201 A3 WO2009012201 A3 WO 2009012201A3 US 2008069934 W US2008069934 W US 2008069934W WO 2009012201 A3 WO2009012201 A3 WO 2009012201A3
Authority
WO
WIPO (PCT)
Prior art keywords
phenyl
preparation
trifluoroalkyl
trifluoroacetylmorpholine
sulfonamide compounds
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2008/069934
Other languages
English (en)
Other versions
WO2009012201A2 (fr
Inventor
Terrence Joseph Connolly
Anita Wai-Yin Chan
Zhixian Ding
Mousumi R Ghosh
Xinxu Shi
Jianxin Ren
Eric Hansen
Roger Farr
Michael Macewan
Asaf Alimardanov
Antonia Nikitenko
John Potoski
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Wyeth LLC
Original Assignee
Wyeth LLC
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wyeth LLC filed Critical Wyeth LLC
Publication of WO2009012201A2 publication Critical patent/WO2009012201A2/fr
Publication of WO2009012201A3 publication Critical patent/WO2009012201A3/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/10—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms
    • C07D295/104—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/108—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by doubly bound oxygen or sulphur atoms with the ring nitrogen atoms and the doubly bound oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/26—Oxygen atoms attached in position 2 with hetero atoms or acyl radicals directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Psychiatry (AREA)
  • Hospice & Palliative Care (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Compounds Containing Sulfur Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Abstract

L'invention concerne un nouvel agent de trifluoroacétylation, à savoir, la N-trifluoroacétylmorpholine. Ce réactif est utilisé dans la préparation de composés de sulfonamides phényliques et hétérocycliques. L'invention concerne également des procédés de préparation de composés de sulfonamides ayant la structure suivante, dans laquelle R1 et R2 sont définis dans la description, au moyen de la N- trifluoroacétylmorpholine. Les composés de sulfonamide qui peuvent être préparés comme spécifié dans la description comprennent l'acide 5-chloro-thiophène-2-sulfonique [(1S,2R)-2-(3,5-difluoro- phényl)-3,3,3-trifluoro-1-hydroxyméthyl-propyl]-amide au moyen de la N- trifluoroacétylmorpholine.Formule (I).
PCT/US2008/069934 2007-07-16 2008-07-14 Procédé de préparation de sulfonamides de trifluoroalkyl-phényle et hétérocycliques Ceased WO2009012201A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US95965907P 2007-07-16 2007-07-16
US60/959,659 2007-07-16

Publications (2)

Publication Number Publication Date
WO2009012201A2 WO2009012201A2 (fr) 2009-01-22
WO2009012201A3 true WO2009012201A3 (fr) 2009-07-02

Family

ID=40260327

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2008/069934 Ceased WO2009012201A2 (fr) 2007-07-16 2008-07-14 Procédé de préparation de sulfonamides de trifluoroalkyl-phényle et hétérocycliques

Country Status (7)

Country Link
US (1) US20090023903A1 (fr)
AR (1) AR067534A1 (fr)
CL (1) CL2008002058A1 (fr)
PA (1) PA8789601A1 (fr)
PE (1) PE20090824A1 (fr)
TW (1) TW200911778A (fr)
WO (1) WO2009012201A2 (fr)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20060002908A (ko) * 2003-03-31 2006-01-09 와이어쓰 베타 아밀로이드 생산 억제제인 플루오로- 및트리플루오로알킬-함유 헤테로사이클릭 설폰아미드 및 이의유도체
US9223217B2 (en) 2010-02-19 2015-12-29 International Business Machines Corporation Sulfonamide-containing topcoat and photoresist additive compositions and methods of use
US9223209B2 (en) * 2010-02-19 2015-12-29 International Business Machines Corporation Sulfonamide-containing photoresist compositions and methods of use
CN102964233A (zh) * 2012-11-18 2013-03-13 大连九信生物化工科技有限公司 一种3,5-二氟三氟甲基苯酮的合成方法
CN103214413B (zh) * 2013-03-22 2015-05-13 郑州泰基鸿诺药物科技有限公司 一种含杂环的三氟甲基酮化合物及其制备方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040198778A1 (en) * 2003-03-31 2004-10-07 Wyeth Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2703802A (en) * 1953-08-20 1955-03-08 Dow Chemical Co 4-(trifluoroacetyl) morpholine
US5461162A (en) * 1994-07-27 1995-10-24 Merck & Co., Inc. Process of synthesizing n-acyl auxiliaries
US5594134A (en) * 1995-03-31 1997-01-14 Merck & Co., Inc. Process of synthesizing N-acyl auxiliaries
JP2004517892A (ja) * 2000-12-13 2004-06-17 ワイス β−アミロイド産生の複素環スルホンアミド阻害剤
KR20050010882A (ko) * 2002-06-11 2005-01-28 와이어쓰 베타 아밀로이드 생산의 치환 페닐술폰아미드 저해제
DE602005016775D1 (de) * 2004-01-16 2009-11-05 Wyeth Corp Heterocyclische, ein azol enthaltende sulfonamidinhibitoren der beta-amyloid-produktion
EP1984321A1 (fr) * 2006-02-17 2008-10-29 Wyeth Méthodes de synthèse d'alcools substitués par sulfonamide et intermédiaires correspondants
AR059517A1 (es) * 2006-02-17 2008-04-09 Wyeth Corp N- sulfonilacion selectiva de alcoholes sustituidos con 2- aminotrifluoralquilo
US7550629B2 (en) * 2006-04-21 2009-06-23 Wyeth Trifluoromethyl-containing phenylsulfonamide beta amyloid inhibitors
US7476762B2 (en) * 2006-04-21 2009-01-13 Wyeth Methods for preparing sulfonamide compounds

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20040198778A1 (en) * 2003-03-31 2004-10-07 Wyeth Fluoro- and trifluoroalkyl-containing heterocyclic sulfonamide inhibitors of beta amyloid production and derivatives thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
M. PAILER AND W.J. HÜBSCH: "Bestimmung von primären und sekundären Aminen in Form von Amiden mit HIilfe der Gaschromatographie auf gepackten und Kapillar-Säulen", MONATSHEFTE FÜR CHEMIE, vol. 97, no. 6, 1966, pages 1541 - 1553, XP002525373 *

Also Published As

Publication number Publication date
PA8789601A1 (es) 2009-02-09
PE20090824A1 (es) 2009-07-24
TW200911778A (en) 2009-03-16
AR067534A1 (es) 2009-10-14
WO2009012201A2 (fr) 2009-01-22
US20090023903A1 (en) 2009-01-22
CL2008002058A1 (es) 2008-11-14

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